[ CAS No. 958-09-8 ] {[proInfo.proName]}

Name: 958-09-8|(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol|98%
Brand: Ambeed
SKU: A159248
Price: 10.0 USD
Availability: InStock
Rating: 99 (29 reviews)

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Cat. No.: {[proInfo.prAm]}

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Quality Control of [ 958-09-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 958-09-8 ]

Product Details of [ 958-09-8 ]

CAS No. :	958-09-8	MDL No. :	MFCD00005754
Formula :	C₁₀H₁₃N₅O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	OLXZPDWKRNYJJZ-RRKCRQDMSA-N
M.W :	251.24	Pubchem ID :	13730
Synonyms :		Chemical Name :	(2R,3S,5R)-5-(6-Amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol

Calculated chemistry of [ 958-09-8 ]

Physicochemical Properties

Num. heavy atoms :	18
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.5
Num. rotatable bonds :	2
Num. H-bond acceptors :	6.0
Num. H-bond donors :	3.0
Molar Refractivity :	61.51
TPSA :	119.31 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-8.22 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.03
Log Po/w (XLOGP3) :	-0.55
Log Po/w (WLOGP) :	-1.27
Log Po/w (MLOGP) :	-1.54
Log Po/w (SILICOS-IT) :	-1.48
Consensus Log Po/w :	-0.76

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-1.29
Solubility :	12.9 mg/ml ; 0.0514 mol/l
Class :	Very soluble
Log S (Ali) :	-1.49
Solubility :	8.21 mg/ml ; 0.0327 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-0.4
Solubility :	100.0 mg/ml ; 0.398 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	3.6

Safety of [ 958-09-8 ]

Signal Word:	Danger	Class:	6.1
Precautionary Statements:	P301+P310	UN#:	2811
Hazard Statements:	H301	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 958-09-8 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 958-09-8 ]
Downstream synthetic route of [ 958-09-8 ]

[ 958-09-8 ] Synthesis Path-Upstream 1~9

1
[ 958-09-8 ]
[ 890-38-0 ]
[ 34371-14-7 ]

Reference： [1] Photochemistry and Photobiology, 1999, vol. 70, # 2, p. 152 - 158

2
[ 958-09-8 ]
[ 64325-78-6 ]

Reference： [1] Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2372 - 2393
[2] Journal of the American Chemical Society, 1982, vol. 104, # 5, p. 1316 - 1319

3
[ 958-09-8 ]
[ 5536-17-4 ]
[ 58-61-7 ]
[ 524-69-6 ]

Reference： [1] Doklady Chemistry, 1987, vol. 296, # 10, p. 431 - 434[2] Dokl. Akad. Nauk SSSR Ser. Khim., 1987, vol. 296, # 4, p. 872 - 876

4
[ 362-75-4 ]
[ 5536-17-4 ]
[ 958-09-8 ]
[ 58-61-7 ]
[ 524-69-6 ]

Reference： [1] Doklady Chemistry, 1987, vol. 296, # 10, p. 431 - 434[2] Dokl. Akad. Nauk SSSR Ser. Khim., 1987, vol. 296, # 4, p. 872 - 876

5
[ 65-85-0 ]
[ 958-09-8 ]
[ 4546-72-9 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2005, vol. 15, # 22, p. 5045 - 5048

6
[ 98-88-4 ]
[ 958-09-8 ]
[ 4546-72-9 ]

Reference： [1] Chemical and Pharmaceutical Bulletin, 1981, vol. 29, # 11, p. 3274 - 3280
[2] Patent: US4667017, 1987, A,
[3] Journal of the American Chemical Society, 2010, vol. 132, # 11, p. 3862 - 3869

7
[ 958-09-8 ]
[ 4546-72-9 ]

Reference： [1] Synthetic Communications, 2003, vol. 33, # 7, p. 1233 - 1243
[2] Nucleosides, Nucleotides and Nucleic Acids, 2002, vol. 21, # 4-5, p. 393 - 400
[3] Tetrahedron, 1997, vol. 53, # 33, p. 11317 - 11346
[4] Helvetica Chimica Acta, 1982, vol. 65, # 8, p. 2372 - 2393
[5] Journal of the American Chemical Society, 1982, vol. 104, # 5, p. 1316 - 1319

8
[ 958-09-8 ]
[ 890-38-0 ]

Reference： [1] Journal of Organic Chemistry, 1995, vol. 60, # 19, p. 6129 - 6134
[2] Helvetica Chimica Acta, 1987, vol. 70, # 6, p. 1649 - 1660
[3] Journal of the American Chemical Society, 1987, vol. 109, # 4, p. 1275 - 1278
[4] Helvetica Chimica Acta, 1999, vol. 82, # 12, p. 2119 - 2129
[5] Bioorganic and Medicinal Chemistry Letters, 2000, vol. 10, # 2, p. 139 - 141
[6] Nucleosides, Nucleotides and Nucleic Acids, 2009, vol. 28, # 5-7, p. 614 - 632
[7] Biochemistry, 2013, vol. 52, # 37, p. 6525 - 6536
[8] Antimicrobial Agents and Chemotherapy, 2013, vol. 57, # 12, p. 6254 - 6264

9
[ 958-09-8 ]
[ 890-38-0 ]
[ 51385-49-0 ]
[ 31077-24-4 ]
[ 3506-01-2 ]
[ 106449-56-3 ]
[ 66224-66-6 ]
[ 117182-88-4 ]

Reference： [1] Journal of Biomolecular Structure and Dynamics, 2012, vol. 30, # 4, p. 394 - 406

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Yield	Reaction Conditions	Operation in experiment
90%	With tetrabutyl ammonium fluoride In tetrahydrofuran
78%	With tetrabutyl ammonium fluoride In tetrahydrofuran at 75℃; for 1h;
	With tetrabutyl ammonium fluoride Yield given;

Yield	Reaction Conditions	Operation in experiment
	With 1,1,1,3,3,3-hexamethyl-disilazane
	With 2,6-dimethylpyridine In N,N-dimethyl-formamide for 1h; Ambient temperature;
	With pyridine for 0.25h;

	With pyridine at 20℃;
	With pyridine for 0.5h; Ambient temperature;
	In pyridine 0 deg C then warmed to r.t. for 1-2 h;
	With triethylamine In pyridine
	With pyridine Ambient temperature;
	With pyridine
	In pyridine Ambient temperature;
	With pyridine for 0.5h;
	With pyridine at 0℃; for 0.5h;
	With pyridine
	With pyridine at 20℃; for 0.333333h;
	With pyridine at 20℃; for 0.5h;
	With pyridine In water at 20℃; for 2h;	Synthesis of N6-Dimethoxytrityl-2'-deoxyadenosine 2'-Deoxynucleoside (10 mmol) was coevaporated three times with pyridine and dried in vacuo for 12 h. Anhydrous pyridine (50 mL) and chlorotrimethylsilane (50 mmol) were added. After the mixture had been stirred at room temperature for 2 h, dimethoxytrityl chloride (3.7 g, 11 mmol) was added. The reaction was stirred overnight (~16 h) at room temperature. Water (60 mL) and aqueous ammonium hydroxide (2 mL, 28-30%) were added and the reaction mixture was stirred for 30 min. The crude product was extracted into dichloromethane The organic layer was washed two times with a 5% aqueous solution of sodium bicarbonate and dried with anhydrous sodium sulfate. The organic layer containing product was filtered from salts and purified by column chromatography using chloroform/pyridine (99.9:0.1) and a gradient of methanol (0-6%). Yield 99%. 1H NMR (DMSO-d6) δ 8.42 (s, 1H), 8.32 (s, 1H), 7.28-7.26 (m, 5H), 7.19 (d, 4H), 6.84 (d, 4H), 6.32 (t, 1H), 5.31 (d, 1H), 5.12 (t, 1H), 3.86-3.84 (m, 1H), 3.71 (s, 6H), 3.61-3.47 (m, 2H), 2,79-2.74 (m, 1H), 2.27-2.22 (m, 1H); 13C NMR (DMSO-d6) δ 157.69, 153.68, 151.16, 148.07, 145.34, 140.37, 137.27, 129.77, 128.39, 127.71, 126.47, 121.05, 113.00, 88.04, 84.12, 70.92, 69.61, 61.83, 54.99; HRMS (FAB) calcd for C31H31N5O5 (M+) 553.2325 found 553.2309.
	With pyridine at 20℃; for 2h;
	With pyridine at 20℃; for 3.75h; Cooling with ice;
	With pyridine In dichloromethane at 0 - 20℃; for 18h;	GP I: N-butanoylation of nucleosides via transient TMS-protection: General procedure: The respective nucleoside (adenosine, guanosine, or 20-deoxyadenosine) was co-evaporatedthree times and then dissolved in anhydrous pyridine (2±5 mL/mmol), and diluted either with thesame volume of THF or double the volume of CH2Cl2. At 0 °C, TMSCl (2.1-9.0 equiv.) was added.The reaction mixture was allowed to warm up to rt and stirred for 5-18 h. Successively, butyrylchloride (1.1 equiv.) was added slowly and the reaction mixture stirred for another 6 h at rt. Cleavageof TMS ethers was promoted by the addition of either 1 M HCl (0.5 mL/mmol) under vigorous stirringfor 5 min, or methanol (2-5 mL/mmol) and stirring at rt for further 12 h. The reaction was terminatedby removal of all volatile components under high vacuum. The crude residue was co-evaporated withtoluene and CH2Cl2 several times, and then taken up in acetonitrile/demin. water. Purification was performed by means of automated RP flash column chromatography on C18 modified silica gel withan acetonitrile gradient in water (0% to 100%).

Yield	Reaction Conditions	Operation in experiment
98%	With pyridine at 20℃; for 12h;
98%	With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃;
96%	With pyridine Ambient temperature;

[ CAS No. 958-09-8 ] {[proInfo.proName]}

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Product Details of [ 958-09-8 ]

Calculated chemistry of [ 958-09-8 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 958-09-8 ]

Application In Synthesis of [ 958-09-8 ]

[ 958-09-8 ] Synthesis Path-Upstream 1~9

[ 958-09-8 ] Synthesis Path-Downstream 1~88

Precautionary Statements-General

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96%	With pyridine for 2h;
92%	With pyridine at 20℃;
82%
81%	With pyridine Reflux;
66%	With pyridine at 20℃; for 4h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
86%	With 1H-imidazole; methanesulfonic acid; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 2h;
77%	With pyridine; dmap; triethylamine for 4h;
68%	With pyridine at 0 - 20℃;

	With pyridine; dmap; triethylamine at 13℃; for 12h;
	Stage #1: 4,4'-dimethoxytrityl chloride; 2'-deoxy-D-adenosine With pyridine; dmap; triethylamine at 20℃; Stage #2: With methanesulfonyl chloride; triethylamine at 20℃; for 2h;	4.D1 Step D1: 2.2 ml of Et3N and 175 mg of DMAP and then 5.25 g of DMTCl are added, at ambient temperature overnight, to 5 g of 2′-deoxyadenine dissolved in pyridine. 2.4 ml of Et3N and 1.27 ml of MsCl are then added to the mixture. After incubation for 2 h at ambient temperature, the mixture is filtered and washed with ethyl acetate. The filtrate is concentrated and dissolved in 75 ml of ethanol, to which is added 1M of NaOH. After refluxing for 1.5 h, the mixture is cooled to ambient temperature and 1M of HCl is added. The ethanol is evaporated off in a rotary evaporator and the residue is extracted with CH2Cl2. After silica gel column purification, the product dATP-D1 is obtained.

Yield	Reaction Conditions	Operation in experiment
99%	With chloro-trimethyl-silane In pyridine at 20℃; for 16h;
99%	Stage #1: 2'-deoxy-D-adenosine With pyridine; chloro-trimethyl-silane at 20℃; for 2h; Stage #2: 4,4'-dimethoxytrityl chloride With pyridine at 20℃; for 16h;
	With chloro-trimethyl-silane Yield given. Multistep reaction;

Yield	Reaction Conditions	Operation in experiment
100%	With pyridine; dmap for 4h; Ambient temperature;
90%	With dmap; triethylamine In acetonitrile for 3h;
85%	With pyridine

85%	With pyridine at 20℃; for 2h;
79%	With pyridine In dichloromethane at 20℃; for 1.5h; Cooling with ice;	Synthesis of 3′,5′-di-O-acetyl-2′-deoxyadenosine (b) To the solution of 2′-deoxyadenosine a (3 g, 11.95 mmol)in 40 mL of anhydrous pyridine 12 mL of acetic anhydride(119.5 mmol) were slowly dropped and the reactionmixture was stirred for 1.5 h at room temperature.Then, after cooling in the ice bath, 10 mL of CH2Cl2were added and the solution was washed with 10 % aq.NaHCO3 (50 mL). The aqueous layer was extracted twicewith 30 mL of chloroform. The combined organic layerswere dried with MgSO4, the drying agent was filtered offand chloroform evaporated under reduced pressure. Theresulting precipitate was three times evaporated with toluene(3 × 15 mL) and purified by crystallization fromethanol to give 3.18 g (9.5 mmol) of acetylated 2′-deoxyadenosineb (yield 79 %), TLC: Rf = 0.66, (CHCl3/MeOH 80:20 v/v). 1H NMR (250 MHz, CDCl3) δ 2.09(s, 3H, CH3COO), 2.14 (s, 3H, CH3COO), 2.62 (ddd,1H, JH2′,H3 = 2.5 Hz, JH2′,H1′ = 5.9 Hz, Jgem = 14.1 Hz,H2′), 2.96 (ddd, 1H, JH2″,H3′ = 6.3 Hz, JH2″,H1′ = 8.1 Hz,Jgem = 14.1 Hz, H2″), 4.32-4.46 (m, 3H, H4′, H5′,H5″), 5.43 (dt, 1H, JH3′,H2′ = JH3′,H4′ = 2.5 Hz,JH3′,H2″ = 6.3 Hz, H3′) 5.85 (bs, 2H, NH-6), 6.46 (dd, JH3′,H2″ = 6.3 Hz, H3′) 5.85 (bs, 2H, NH-6), 6.46 (dd,1H, JH1′,H2′ = 5.9 Hz, JH1′,H2″ = 8.1 Hz, H1), 7.99 (s, 1H,H2), 8.36 (s, 1H, H8).
75%	In pyridine
74%	With pyridine 1.) 0 deg C, 1 h, 2.) 25 deg C, 5 h;
	Stage #1: acetic anhydride; 2'-deoxy-D-adenosine With pyridine Heating; Stage #2: In methanol at 105℃; for 1.5h;
	With pyridine; dmap for 4h;
	With pyridine
	With dmap; trimethylamine In acetonitrile for 8h; Reflux;	148 First step, a mixture of 2-deoxy-adenosine(3.6 g), acetic anhydride (5.47 g), trimethyl (4.07 g) and DMAP (0.16 g) in anhydrous acetonitrile (40 ml) was refluxed for 8 h. Acetonitrile was removed under reduced pressure. H2O (40 ml) was added to the residue, and the resulting solution was extracted with EtOAc (3 × 40 ml). The EtOAc of the combined organic layer was dried with sodium acetate and The EtOAc layer was filtered and the filtrate was concentrated. The residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (100 : 1) to yield 3',5'-diacetyl-2'-deoxy-adenosine (4.0 g). Second step, a mixture of 3', 5'- diacetyl-2'-deoxy-adenosine(1.2 g), tert-butyl nitrite (7.42 g), and tribromomethane (20 ml) was refluxed for 2 h. The excess tert-butyl nitrite was removed under reduced pressure. The residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (80 : 1) to yield 3',5'-diacetyl-2'-deoxy-6-bromo-adenosine (595 mg). Third step, a mixture of 3', 5'- diacetyl-2'-deoxy-6-bromo-adenosine (398 mg), 3-methoxy-4-hydroxybenzylamine (379.3 mg, the hydrochloride) and triethylamine (253 mg) in anhydrous EtOH (20 ml) was refluxed for 5 h. After evaporation, the residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (50 : 1) to yield N6-(3-methoxy-4-hydroxy-benzyl)-2-deoxy-3, 5'-diacetyl adenosine (340 mg): 1H NMR (300 MHz, acetone-d6):the 2-deoxy- adenosine moiety δ 8.29 (1H, s, H-8), 8.16 (1H, s, H-2), 7.33 (1H, t, J= 6.0 Hz, NH), 6.44 (1H, dd, J= 7.8, 6.3 Hz, H-1), 5.48 (1H, m, H-3'), 4.36 (1H, dd, J= 6.3, 12.9 Hz, H-5'a), 4.30 (1H, dd, J= 6.0, 12.9 Hz, H-5'b), 4.29 (1H, m, H-4'), 3.21 (1H, ddd, J= 7.5, 7.8, 15.0 Hz, H-2'a), 2.59 (1H, ddd, J = 2.4, 6.0, 15.0, H-2'b); the 3-methoxy-4-hydroxybenzyl moiety δ 7.63 (1H, brs, OH), 7.05 (1H, d, J= 1.5 Hz, H-2"), 6.87 (1H, dd, J= 7.8, 1.5 Hz, H-6"), 6.74 (1H, d, J= 7.8 Hz, H-5"), 4.76 (2H, brs, H-7"), 3.75 (3H, s, OMe); the acetyl δ2.09 (3H, s, CH3CO), 2.01 (3H, s, CH3CO); 13C NMR (300 MHz, acetone-d6):the 2-deoxy- adenosine moiety δ 155.9 (C-6), 153.6 (C-2), 149.1 (C-4), 139.9 (C-8), 121.2 (C-5), 85.2 (C-1), 83.1 (C-4'), 75.6 (C-3'), 64.5 (C-5'), 37.0 (C-2'); the 3-methoxy-4-hydroxy moiety δ 148.2 (C-3"), 146.5 (C-4"), 132.0 (C-1), 121.2 (C-2"), 115.6 (C-6"), 112.3 (C-5"), 56.1 (OMe), 44.2 (C-7"); the acetyl δ170.8, 170.7, 20.9, 20.6ο
4.0 g	With dmap In acetonitrile for 8h; Reflux;	148 First step, a mixture of 2'-deoxy-adenosine (3.6 g), acetic anhydride (5.47 g), trimethyl (4.07 g) and DMAP (0.16 g) in anhydrous acetonitrile (40 ml) was refluxed for 8 h. Acetonitrile was removed under reduced pressure. H2O (40 ml) was added to the residue, and the resulting solution was extracted with EtOAc (3*40 ml). The EtOAc of the combined organic layer was dried with sodium acetate and The EtOAc layer was filtered and the filtrate was concentrated. The residue was separated by column chromatography over silica gel and eluted with CHCl3-CH3OH (100:1) to yield 3',5'-diacetyl-2'-deoxy-adenosine (4.0 g).
	With pyridine; dmap at 20℃; for 4h;

Yield	Reaction Conditions	Operation in experiment
99%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃;
98%	With 1H-imidazole In N,N-dimethyl-formamide for 15h;
96%	With 1H-imidazole In N,N-dimethyl-formamide at 35℃; for 16h;

95%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃;
95%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 8h; Inert atmosphere;
95%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 14h;	Synthesis of 3',5'-O-bis(TBS)-2'-deoxyadenosine [11] Synthesis was performed according to the method described in the literature, using 2'-deoxyadenosine (10) as a starting material. 1H NMR spectrum was consistent with the literature value.
92%	With 1H-imidazole In N,N-dimethyl-formamide at 60℃; for 1h;
87.3%	With pyridine; 1H-imidazole at 20℃; for 24h; Inert atmosphere;
84%	With 1H-imidazole; dmap In N,N-dimethyl-formamide for 0.5h;
84%	With 1H-imidazole In N,N-dimethyl-formamide at 0℃; for 0.5h;	42.a To a solution of 2-deoxyadenosine (3.00 g, 11.1 mmol, 1.0 equiv) in DMF (16 mL) at 0° C. were added imidazole (4.54 g, 66.8 mmol, 6.0 equiv) and DMAP (200 mg, 1.6 mmol, 0.15 equiv). Next, a solution of TBSCI (4.20 g, 27.9 mmol, 2.5 equiv) in DMF (8.0 mL) was added dropwise at 0° C. and the reaction stirred 30 minutes. The reaction mixture was diluted with saturated aqueous NaHCO3 (100 mL) and extracted with EtOAc (3×100 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under reduced pressure. Purification by flash chromatography (6:1 EtOAc/hexanes) afforded the title compound (4.5 g, 84%) as a white solid: mp 123-125° C.; Rf 0.7 (1:3 EtOAc/hexanes); [α]20D -2.7 (c 0.96, CHCl3); 1H NMR (600 MHz, CDCl3) δ 0.00 (s, 6H), 0.01 (s, 6H), 0.82 (s, 18H), 2.34 (ddd, J=13.2, 6.0, 4.2 Hz, 1H), 2.50-2.58 (m, 1H), 3.68 (dd, J=10.8, 3.0 Hz, 1H), 3.78 (dd, J=11.4, 4.2 Hz, 1H), 3.92 (dd, J=6.6, 3.0 Hz, 1H), 4.52 (dd, J=9.0, 3.6 Hz, 1H), 5.70 (br s, 2H), 6.36 (t, J=6.6 Hz, 1H), 8.05 (s, 1H), 8.26 (s, 1H); 13C NMR (150 MHz, CDCl3) δ -5.5, -5.4, -4.1, -4.7, 18.0, 18.4, 25.8, 26.0, 41.3, 62.8, 71.9, 84.3, 87.9, 120.0, 139.1, 149.6, 152.8, 155.3; HRMS (ESI+) calcd for C22H40N5O3Si2 [M-H]+ 478.2664, found 478.2656 (error 1.7 ppm).
80%	With 1H-imidazole; dmap In N,N-dimethyl-formamide at 20℃; Inert atmosphere;	1 1.2 tert-butyldimethylsilyl chloride (TBDMSCI, 2.5 mmol) was added to a solution of dry nucleoside (1.0 mmol), dimethyl aminopridine (DMAP, 0.15 mmol) and imidazole (6 mmol) in anhydrous DMF (10 mL). After the reaction mixture was stirred overnight at room temperature under nitrogen, it was quenched with sat. aq. NaHCO3, and extracted with dichloromethane. The combined organic layer was concentrated, and the residue was purified by silica gel flash chromatography with a gradient eluent of CH2Cl2-CH3OH from 100:0 to 100:5. 3',5'-Bis-O-(tert-butyldimethylsilyl)-deoxyadenosine (1): yield 80%. 1H NMR (500 MHz, CDCl3): δ 8.29 (s, 1H, 2-H), 8.09 (s, 1H, 8-H), 6.65 (br s, 2H, NH2), 6.41 (t, 1H, 1'-H), 4.56 (dd, 1H, 3'-H), 3.96 (d, 1H, 4'-H), 3.82 (dd, 1H, 5'-H), 3.72 (dd, 1H, 5"-H), 2.59 (m, 1H, 2'-H), 2.39 (m, 1H, 2"-H), 0.86 (s, 18H, (CH3)3CSi), 0.05 (s, 6H, CH3SiO), 0.03 (s, 6H, CH3SiO). HRMS (APCI): calcd for C22H41N5O3Si2+H, -480.2826. found, 480.2818.
78%	With 1H-imidazole In N,N-dimethyl-formamide
73%	With triethylamine In N,N-dimethyl-formamide at 20℃; for 3h;
58%	With pyridine; dmap; 4 A molecular sieve for 72h;
	With 1H-imidazole; acetic acid 1.) pyridine, room temperature, 2 d, 2.) room temperature, 30 min; Yield given. Multistep reaction;
	With 1H-imidazole In N,N-dimethyl-formamide
	With 1H-imidazole In N,N-dimethyl-formamide
	Stage #1: 2'-deoxy-D-adenosine With 1H-imidazole In N,N-dimethyl-formamide for 0.25h; Cooling with ice; Stage #2: tert-butyldimethylsilyl chloride In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 24.0833h;	2.1 An anhydrous mixture of dA (10, 10 g), imidazole (4.1 g), and DMF (150 mL) was placed under a dry atmosphere and cooled in an ice/water bath for 15 minutes. A solution of TBDMS-C1 (9 g) in anhydrous THF (25 mL) was added over 5 minutes. The resulting mixture was stirred at room temperature for 24 hours. The solution was concentrated in vacuo and the residual syrup was partitioned between EtOAc (300 mL), Hexane (30 mL), and water (300 mL). The layers were separated, and the organic layer was washed with 10% aqueous sodium bicarbonate (2 X 300 mL), dried over dried over anhydrous sodium sulfate, filtered, and concentrated at reduced pressure. The solid was triturated with hexanes, filtered, and dried in vacuo to afford 11a. TLC (silica gel on glass, 50EtOAc:50DCM) shows a single spot, Rf = 0.30.
	With 1H-imidazole In N,N-dimethyl-formamide	5 The synthesis of 27 commences with commercially available deoxyadenosine 22 which is silylated at both hydroxyl groups furnishing 23. The NPOM caging group is installed on N-6 using NaH as the base in DMF. Converting N-6 into a secondary amine (as in 24) has been shown to be sufficient as a protecting strategy for chemical DNA synthesis. The TBDMS groups is subsequently removed by treatment with NH4F and the 5'-OH in 25 is selectively blocked by DMT protection leading to 26. The synthesis of 27 is completed through phosphoramidite formation.

75%	With 1H-imidazole In N,N-dimethyl-formamide at 20℃; for 4h;	40.a; 96.a Example 40: ((2R,3S,4R,5R)-5-{4-[(lS)-2,3-Dihydro4H-inden-l-ylamino]-7H-pyrrolo[2,3-2SO4 and concentrated in vacuo. The product was isolated as a white solid (4.138 g, 75 %) and was used without further purification.[0304] LCMS: R.t. 1.31 min, ES+ 366 (formic acid).; Example 96: [(2R,3S,5R)-3-hydroxy-5-(6-phenyl-9H-purin-9-yl)tetrahydrofuran-2-yl]- methyl sulfamate (1-93)Step a: (2R3S,5R)-5-(6-amino-9I-purin-9-yl)-2-({ rtert-butyl(dimethyl)silyl1oxy tmethyl)- tetrahydrofuran-3-ol[0709] To a solution of dry (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(hydroxymethyl)tetrahydrofuran-3-ol (3.78 g, 15.04 mmol) and imidazole (2.46 g, 36.1 mmol) in DMF (20 mL) was added TBSCl (2.38 g, 15.80 mmol) and the solution was stirred at r.t. for 4 hours. The reaction mixture was diluted with water (100 mL), and extracted with EtOAc (3 x 100 mL). The combined organics were dried (Na2SO4)and concentrated. The product was isolated as a white solid (4.138 g, 75%) and was used without further purification.[0710] LCMS: R.t. 1.31 min ES+ 366 (formic acid)
72%	With pyridine; 1H-imidazole In N,N-dimethyl-formamide at 20℃;
48%	In N,N-dimethyl-formamide at 25℃; for 12h;	11.1 Step 1: preparation of compound 11b To a solution of compound ha (4.1 g, 16.383 mmol, 1.0 eq) in pyridine (50 mL) was added 4-dimethylaminopyridine (0.4 g, 3.277 mmol, 0.2 eq) and tert-butyldimethylsilylchloride (3.704 g, 24.575 mmol, 1.5 eq) at 25 °C. Then the reaction mixture was stirred at25 °C for 12 h. The solvent was concentrated under reduced pressure to give a residuethat was purified by column chromatography on silica gel (DCM/MeOH=50/1 to 10/1) toafford compound llb (2.86 g, 48 % yield) as a white solid. ‘H NIVIR (400 MHz, CD3OD)8.32 (s, 1H), 8.21 (s, 1H), 6.47 (dd, J=5.2, 7.2 Hz, 1H), 4.31 - 4.18 (m, 2H), 4.06 - 3.96(m, 1H), 3.94 - 3.84 (m, 1H), 3.18 - 3.06 (m, 1H), 2.80 - 2.70 (m, 1H), 0.85 (s, 9H), 0.03 (d, J9.6 Hz, 6H); ESI-MS m/z 365.1 [M+lfb.
	With pyridine cooling;
	With pyridine at 20℃; for 4h;

Yield	Reaction Conditions	Operation in experiment
52%	With PS lipase In tetrahydrofuran at 30℃;
52%	With PSL lipase In tetrahydrofuran at 30℃; for 60h; Yields of byproduct given;
28%	With Pseudomonas fluorescence lipase In tetrahydrofuran at 30℃; for 36h;

Yield	Reaction Conditions	Operation in experiment
78%	In tetrahydrofuran at 30℃; for 8h; lipase from C_. antarctica;
75%	With CA lipase In tetrahydrofuran at 5℃;
	With Candida antarctica lipase B In tetrahydrofuran at 45℃;

Yield	Reaction Conditions	Operation in experiment
65%	With pyridine at -5℃;
62%	With pyridine; dmap In dichloromethane at 0℃; for 3h;
37%	With pyridine at 0℃;

18%	With pyridine at 0℃; for 96h; Inert atmosphere;
	With pyridine at 0℃; for 16h;

Yield	Reaction Conditions	Operation in experiment
91%	With pyridine
88%	With pyridine at 20℃; for 18h; Inert atmosphere;
84%	With pyridine; 1H-imidazole at 20℃;

80%	With pyridine; dmap; triethylamine for 48h; Ambient temperature;
75%	With pyridine at 22 - 25℃;
72%	regioselective reaction;
63%	With pyridine; 1H-imidazole In N,N-dimethyl-formamide for 2h;	16.1.1 . 1.1 Interemediate 16-i 2 '-Deoxy adenosine (15.0 g,58.5 mmol, 1.0 equiv.) and imidazole (9.96 g, 146 mmol, 2.5 equiv.) were dissolved in dry pyridine (100 mL) and concentrated in vacuo. The resulting mixture was dissolved in anhydrous DMF (75 mL), TBDPSC1 (16.3 mL, 61.4 mmol, 1.1 equiv.) was added, and the mixture was stirred for 2 h. The solution was concentrated in vacuo then dissolved in EtOAc (500 mL), and washed with water (2 x 250 mL), then brine (250 mL). The organic layer was dried over MgS04, filtered, and concentrated in vacuo to afford a thick oil that was purified by flash column (0920) chromatography over silica gel (0% to 5% MeOH in EtOAc) to afford the product as a white solid 16-i (18.0 g, 63%) spectral characteristics consistent with the literature (Krishnakumar, K., et ah, Synlett 7, 1055-1058 (2010)).
12%	With 1H-imidazole In dichloromethane at 20℃; for 48h; Inert atmosphere;	17E Example 17E: (2R,3S,5R)-5-(6-amino-9H-purin-9-yl)-2-(((tert-butyldiphenylsilyl)oxy)methyl)tetrahydrofuran-3-ol TBDPS-CI (1.8 mL, 7.06 mmol) was added dropwise over 40 minutes to a stirred suspension of 2-deoxyadenosine monohydrate (2.0 g, 7.43 mmol) and imidazole (1.52 g, 22.3 mmol) in DCM (100 mL) under a nitrogen atmosphere. The resulting white suspension was stirred at room temperature for 2 days. Water (50 mL) was added and the mixture extracted with DCM (3 x 100mL). The combined organic extracts were dried (Na2S04) and the solvent evaporated in vacuo to leave a colourless oil. This was purified by flash column chromatography using an increasing gradient from 50-100% EtOAc/hexane then 2-10% MeOH/EtOAc to give the product (430 mg, 0.88 mmol, 12%) as a white foam. UPLC-MS (Acidic 2 min): rt 1.00 min, m/z 490 [M+H]+H NMR (400 MHz, CDCI3) δ ppm: H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.06 (s, 9 H) 2.49 - 2.57 (m, 1 H) 2.75 (dd, J^13.30, 6.65 Hz, 1 H) 3.82 - 3.95 (m, 2 H) 4.04 - 4.15 (m, 1 H) 4.71 - 4.75 (m, 1 H) 5.73 (br s, 2 H) 6.45 (t, J=6.46 Hz, 1 H) 7.11 (s, 1 H) 7.33 - 7.45 (m, 6 H) 7.60 - 7.66 (m, 4 H) 8.02 (s, 1 H) 8.29 (s, 1 H)
	With 1H-imidazole In pyridine at 20℃; for 5h;
	With pyridine for 24h; Ambient temperature;
	With pyridine at 20℃;
	With 1H-imidazole In N,N-dimethyl-formamide

Yield	Reaction Conditions	Operation in experiment
100%	With 3-chloro-benzenecarboperoxoic acid In methanol Ambient temperature;
90%	With 3-chloro-benzenecarboperoxoic acid In methanol for 5h; Ambient temperature;
	With 3-chloro-benzenecarboperoxoic acid In methanol at 30℃; for 7h;

	With 3-chloro-benzenecarboperoxoic acid In methanol; water for 16h; Ambient temperature;
	Multi-step reaction with 2 steps 1: 78 percent / 1.) dinitrophenoxyamine, 2.) aq. HCl / dimethylformamide / 24 h / 37 °C 2: 84 percent / hydroxylamine, aq. NaOH / 48 h / 50 °C

Yield	Reaction Conditions	Operation in experiment
100%	With bromine; sodium acetate; acetic acid In water at 20 - 50℃;
88%	With bromine; sodium acetate
88%	With sodium azide; bromoisocyanuric acid monosodium salt In water; N,N-dimethyl-formamide at 20℃; for 0.5h;	General procedure: 5'-O-Monomethoxytrityl-N2-phenoxyacetylguanosine (33, 0.138 g, 0.2 mmol) was dissolved inaqueous DMF solution (H2O:DMF 1:4, 5 mL) under stirring. SMBI (1.1 equiv., 0.051 g, 0.22 mmol)was added at r.t. and the mixture stirred. Progress of the reaction was followed by TLC. An additionalamount of the reagent (0.15 equiv., 0.007 g) was added into the reaction mixture after 1.5 h. Oncompletion of the reaction by 2 h, the reaction mixture was filtered, evaporated to dryness underreduced pressure and coevaporated with water (2 × 2 mL). The crude reaction mixture was purified bycolumn chromatography (4%-5% MeOH in DCM, v/v) to afford nucleoside 34 (0.148 g, 96%) in pureform as a white solid.8-Bromo-5'-O-monomethoxytrityl-N2-phenoxyacetylguanosine (34).

83%	With bromine at 20℃; for 16h; aq. acetate buffer;
82%	With bromine In acetate buffer at 20℃;
81%	With bromine; sodium acetate at 20℃; aq. acetate buffer;
81%	With bromine In aq. acetate buffer at 20℃; for 18h;
79%	With bromine In acetate buffer at 20℃; for 4h;
75.5%	With bromine In 1,4-dioxane at 20℃;
69%	With bromine In aq. acetate buffer at 20℃; for 3h;
68%	With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at 25℃; for 3.5h;	Typical procedure for the bromination of unprotected nucleosides: DBH (323 mg, 1.13 mmol) was added to a stirred solution of 1d (500 mg, 2.05 mmol) in DMF (5 mL). The resulting pale-yellow solution was stirred at room temperature for 20 minutes or until TLC showed absence of starting material and formation of less polar product. Volatiles were evaporated and the residue was coevaporated with MeCN. The resulting pale solid was crystallized from hot acetone to give 2d (500 mg, 75%) as colorless crystals with data as reported.14
67%	With bromine
61%	With bromoisocyanuric acid monosodium salt In water; N,N-dimethyl-formamide at 25℃; for 1.5h; Inert atmosphere;
40%	With N-Bromosuccinimide In N,N-dimethyl-formamide for 12h; Ambient temperature;
40%	With bromine; sodium acetate In water
34%	With bromine In water for 3h;
30.4%	With bromine In water at 20℃; for 24h; Heating;
25%	With N-Bromosuccinimide In methanol at 40℃; for 18h;	8 Synthesis of Compound (16) (8-bromo-2'-deoxyadenosine) To a solution of deoxyadenosine (15) (3 g, 11 mmol) in methanol (50 ml) was added NBS (2.6 g, 14.6 mmol, 1.3 eq.). The mixture was stirred at 40° C. for 18 h. The pink suspension was filtered, and the filtrate was dried in vacuo to yield compound (16) (900 mg, 25%) as a pink solid.
	With bromine; sodium acetate
	With bromine; sodium acetate
	With bromine; sodium acetate; acetic acid at 20℃; for 12h;
	With bromine; sodium acetate; acetic acid In water
	With bromine In acetate buffer at 20℃; for 3h;
	With bromine at 20℃; for 3h; aq. acetate buffer;
	With bromine; acetic acid In 1,4-dioxane; water at 20℃; for 12h; Inert atmosphere;

Yield	Reaction Conditions	Operation in experiment
88%	With pyridine at 100℃; for 24h;
62%	Stage #1: N,N'-bis(dimethylaminomethylene)hydrazine; 2'-deoxy-D-adenosine With pyridine; chloro-trimethyl-silane for 21h; Stage #2: With methanol for 6h; Heating;

Yield	Reaction Conditions	Operation in experiment
92%	In water at 30℃; for 12h;
83%	With sodium hydrogencarbonate In tetrahydrofuran at 20℃; for 96h;
77%	Stage #1: 2'-deoxy-D-adenosine In water at 20℃; for 0.25h; Stage #2: 2-chloroethanal With sodium hydroxide In water for 28h;

70%	With sodium acetate at 20℃; for 70h;
70%	In water at 20 - 50℃; for 70h; Sodium acetate buffer;	1 Example 1 3-(2-Deoxy-β-D-erythro-pentofuranosyl)-3H-imidazo[2,1-i]purine (N1,N6-Etheno-2'-deoxyadenosine (5)). 2'-Deoxyadenosine monohydrate (1) (5.0 g, 20 mmol) was dissolved in 1M aq. sodium acetate buffer (pH 4.5 - 5.0, 110 mL) by warming to 40 - 50°C. To the solution chloroacetaldehyde (50% aq. soln, 7.7 mol/L, 25 mL) was added, and the reaction mixture was stirred for 70 h at room temperature. The yellow solution was evaporated to dryness, and the residue was dissolved in MeOH and filtered to remove inorganic salt. After washing with MeOH the combined filtrate and washings were concentrated in vacuo at 40 - 50°C. The residue was applied to FC (silica gel 60H, column: 20 x 6 cm). Elution with CH2Cl2-MeOH (85:15) gave a main fraction from which upon evaporation of the solvent and subsequent crystallization from MeOH-EtOAc compd. 5 (3.86 g, 70%) was isolated as colorless crystals. M.p. 138-141°C. TLC (silica gel, EtOAc-MeOH, 3:1): Rf 0.4. UV (MeOH): λmax 275 (7300), 265 (7600), 258 (6600), 229 nm (35700). 1H-NMR ([D6]DMSO) δ 2.39 (m, 1H, Hα-C(2')); 2.70 (m, 1H, Hβ-C(2')); 3.57 (m, 1H, Ha-C(5')); 3.67 (m, 1H, Hb-C(5')); 3.88 (m, 1H, H-C(4'); 4.43 (m, 1H, H-C(3')); 4.99 (t, 1H, 3J(H,H) = 5.2 Hz, 5'-OH); 5.38 (d, 1H, 3J(H,H) = 3.8 Hz, 3'-OH); 6.47 (pt, 1H, 3J(H,H) = 6.2 Hz, H-C(1')); 7.55 (s, 1H, H-C(11); 8.07 (s,1H, H-C(10); 8.53 (s, 1H, H-C(2)); 9.29 (s, 1H, H-C(8)).
	With aq. buffer (pH=4.5)
	In aq. phosphate buffer at 100℃; for 0.25h;

Yield	Reaction Conditions	Operation in experiment
100%	With water-d2; triethylamine at 65℃; for 65h;
60%	With [⁽²⁾H₆]acetone; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 1h;
	With water-d2 at 90℃; for 5h;

	With water-d2 at 100℃; for 6h;
	With water-d2; triethylamine

Yield	Reaction Conditions	Operation in experiment
77%	With Enterobacter gergoviae CECT 875 in agarose In phosphate buffer at 60℃; for 1h; Enzymatic reaction;
67%	With Citrobacter koseri In aq. phosphate buffer at 60℃; for 1h; Microbiological reaction;
	With aeromonas hydrophila CECT 4221 at 60℃; for 4h; aq. phosphate buffer; Enzymatic reaction;

	With Bacillus psychrosaccharolyticus CECT 4074 nucleoside 2'-deoxyribosyltransferase In aq. buffer at 40℃; for 0.0833333h; Enzymatic reaction;	N-Deoxyribosyltransferase Assay for Soluble BpNDT General procedure: The standard activity assay was performed by incubating 5 μL of cell extract or 0.40 μg of pure enzyme with 10 mM deoxyuridine and 10 mM adenine in 50 mM HEPES buffer, pH 8.0 in a final volume of 40 μL. The reaction mixture was incubating at 40 °C, 30 r.p.m., for 5 min. Then, activity was stopped by addition of 40 μL of cold methanol in ice-bath and heating for 5 min at 95 °C as described for others NDTs [9]. After centrifugation at 9000 ×g for 2 min, samples were half-diluted with water and the nucleoside production was measured at 254 nm by HPLC (Agilent 1100 series) with an ACE 5 μm C18-PFP column 250 mm × 46 mm (Advanced Chromatography Technologies) equilibrated with 100% trimethyl ammonium acetate at a flow rate of 1 mL/min. Elution was carried out by a discontinuous gradient: 0-10 min, 100% to 90% trimethyl ammonium acetate and 0% to 10% acetonitrile, and 10-20 min, 90% to 100% trimethyl ammonium acetate and 10% to 0% acetonitrile. Enzymatic synthesis of natural nucleosides was carried out at standard conditions described above using 10 mM of different 2'-deoxyribonucleosides and bases. Retention times for the reference natural compounds were as follows: uracil (Ura): 5.41 min; 2'-deoxyuridine (dUrd): 9.16 min; adenine (Ade): 10.14 min; 2'-deoxyadenosine (dAdo): 15.50 min; hypoxanthine (Hyp): 7.34 min; 2'-deoxyinosine (dIno): 10.95 min; thymine (Thy): 9.13 min; thymidine (Thd): 13.25; uric acid (UAc): 3.50 min. All determinations were carried out by triplicate and the maximum error was below 5%. In such conditions, one international activity unit (IU) was defined as the amount of enzyme producing 1 μmol/min of 2'-deoxyadenosine under the assay conditions.
	With purine nucleoside phosphorylase; thymidine phosphorylase; phosphoric acid In aq. phosphate buffer at 37℃; for 24h; Enzymatic reaction;	10 (Reference Examples 1 to 28) General procedure: In a 1.5 mL tube, 50 μL (pH 6.8) of a phosphate buffer solution,Raw materials Nucleoside compound 50 mM (each manufactured by Sigma),The target nucleoside compound base (see Table 2) 50 mM,Nucleoside phosphorylase (thymidine phosphorylase,Purine nucleoside phosphorylase, each manufactured by Sigma), 950 μL of waterWas obtained. The final concentration of phosphoric acid and the amount of enzyme are listed in Table 2.The mixture was allowed to react in a warm water bath at 37 ° C. for 24 hours,A small amount of the mixed solution after the reaction was separated and measured by HPLC,The amount of target nucleoside compound produced was confirmed.Table 2 shows the compound used in the reaction,And raw material nucleoside compound(Mol%) of the nucleoside compound to be produced.
	With silica immobilized uridine phosphorylase from Clostridium perfringens and purine nucleoside phosphorylase from Aeromonas hydrophila In methanol; aq. phosphate buffer at 37℃; Flow reactor; Enzymatic reaction;
	With Clostridium perfringens uridine phosphorylase; Aeromonas hydrophila purine nucleosidephosphorylase co-immobilized on glyoxyl-agarose In aq. phosphate buffer at 28℃; Flow reactor; Green chemistry; Enzymatic reaction;	3.9. General Procedure for the Flow Transglycosylation Reaction General procedure: A solution of the sugar donor and the sugar acceptor was prepared in 50mMphosphate buer pH7.5. In the case of hypoxanthine (6), in order to dissolve it, the suspension was sonicated (3 10 min).The temperature was set at 28 C. The column packed with immobilized CpUP and AhPNP (0.68 g,0.68 mL) was washed with 50 mM phosphate buer pH 7.5 at 0.2 mL min1 for 10 min at atmosphericpressure. The substrate solution (2.0 mL) was flowed through the bioreactor. Residence times andconcentrations were varied as reported in Table 1. The reaction outcome was monitored by HPLC. Asample of the exiting flow stream (200 L) was diluted with a mixture of H2O/MeOH (9:1), in order toobtain a sample concentration of 0.1 mM, and was used for the analysis.

Yield	Reaction Conditions	Operation in experiment
87%	With nucleoside deoxyribosyltransferase-II; sodium citrate at 40℃; for 20h; Enzymatic reaction;
	With purine nucleoside phosphorylase; thymidine phosphorylase; phosphoric acid In aq. phosphate buffer at 37℃; for 24h; Enzymatic reaction;	7 (Reference Examples 1 to 28) General procedure: In a 1.5 mL tube, 50 μL (pH 6.8) of a phosphate buffer solution,Raw materials Nucleoside compound 50 mM (each manufactured by Sigma),The target nucleoside compound base (see Table 2) 50 mM,Nucleoside phosphorylase (thymidine phosphorylase,Purine nucleoside phosphorylase, each manufactured by Sigma), 950 μL of waterWas obtained. The final concentration of phosphoric acid and the amount of enzyme are listed in Table 2.The mixture was allowed to react in a warm water bath at 37 ° C. for 24 hours,A small amount of the mixed solution after the reaction was separated and measured by HPLC,The amount of target nucleoside compound produced was confirmed.Table 2 shows the compound used in the reaction,And raw material nucleoside compound(Mol%) of the nucleoside compound to be produced.
	With recobinant purine nucleoside phosphorylase from Escherichia coli; recombinant thymidine phosphorylase from Escherichia coli In aq. phosphate buffer for 8h; Heating; Enzymatic reaction;

Yield	Reaction Conditions	Operation in experiment
81%	With hydrogen; water-d2 at 160℃; for 24h;
81%	With water-d2 at 110℃; for 24h;
	With deuterium In water-d2 at 55℃; for 36h; Glovebox;

Yield	Reaction Conditions	Operation in experiment
84%	With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 13h;
65%	With piperidine; copper(l) iodide; palladium diacetate; caesium carbonate In N,N-dimethyl-formamide at 80℃; for 15h; Inert atmosphere;
52%	With copper(l) iodide; caesium carbonate In N,N-dimethyl-formamide at 60℃; for 15h; Inert atmosphere; Schlenk technique;	General procedure for C8-arylation of 2'-deoxyadenosine 10 at 60 °C 2'-Deoxyadenosine (251 mg, 1.0 mmol, 1.0 equiv), CuI (571 mg, 3.0 mmol, 3 equiv), caesium carbonate (815 mg, 2.5 mmol, 2.5 equiv) and Pd catalyst (mol %) were added to a Schlenk under a N2 atmosphere. DMF (5.3 mL) and the aryl iodide (2.0 mmol, 2.0 equiv) were added and the reaction was stirred at 60 °C for either 24 or 48 h. The reaction was then cooled to room temperature, and HCl (5.3 mL, 1 M) was added to acidify the crude mixture. The pH was tested, and NaOH (1 M) was added until the pH reached 6.5. The reaction mixture was then extracted with EtOAc/iPrOH (5*25 mL, 9:1 v/v), dried over MgSO4 and the solvent removed in vacuo. The crude product was redissolved in MeOH/CH2Cl2 (1:1 v/v) and absorbed onto silica. The product was then purified by column chromatography on silica gel, eluting with MeOH/CH2Cl2 (2:98→1:9 v/v). The solvent was removed in vacuo to yield the pure product. The characterisation data for compound 12 (and 14, 16 and 18) has previously been reported by us. 32

Yield	Reaction Conditions	Operation in experiment
95%	In pyridine at 65℃; for 4h;
93%	With pyridine at 80℃; for 4h;	4.2. N,N-Dibenzoyl-3′,5′-dibenzoyl-2′-deoxyadenosine (5) Benzoyl chloride (6.29 g, 44.74 mmol) was added dropwise to a suspensionof 2′-deoxyadenosine (2.00 g, 7.99 mmol) in pyridine (20 mL) at 0 °C. Tocomplete the reaction, the mixture was stirred and heated to 80 °C for4 h. Then the solvent was removed in vacuo. The resulting residue wasdissolved in CH2Cl2 (100 mL) and washed with H2O (100 mL). The aqueouslayer was extracted with CH2Cl2 (3 × 50 mL). The combined organic layerswere washed with brine (100 mL), dried on anhydrous Na2SO4 and concentratedin vacuo. The resulting residue was recrystallized from EtOH togive 5 (3.84 g, 72% yield) as a white solid.